Wet, I'm impressed. Did you choose your TFL handle due to your bear hunting experiences?
My take is very simple. I read. The difference beween a 41 or 44 mag in a revolver is substantial as compared to 357 mag. Unless you already own the 357 mag, I do't know why someone would choose that caliber over a 41 or 44 for hunting.
As a young hunter, I always supported theory that shot placement was everything and I chose my rifle calibers accordingly in the Eastern woods. I scoffed at the need for a 30-06 (or larger) for deer hunting and the 30-30 ballistics were boring. I moved to a 270 win for my deer hunting over a 243 because having a little more power is helpful in putting the animal down quickly and humanely. But that 270 choice still leaned toward the shot placement over bullet mass approach. Been comfortable with the choice over the years but really don't use a rifle much anymore for deer hunting.
I take this experience to handgun hunting and a 30-30 is a great choice with a Contender. Does that make any sense at all? But I feel if you have the choice available to you, you should choose something a little larger than 357 mag for deer and black bear hunting.
The availability of the hard cast bullets/loads in 357 mag has changed the game somewhat just like pretty good bullets for the 223 has changed the rifle hunting game with deer. But I would still choose something a little larger.